Skip to main content
Log in

Preparation of β-cyclodextrin/dopamine hydrochloride-graphene oxide and its adsorption properties for sulfonamide antibiotics

  • Research Article
  • Published:
Environmental Science and Pollution Research Aims and scope Submit manuscript

Abstract

To develop high-efficiency antibiotic adsorbents, β-cyclodextrin and dopamine hydrochloride were used to modify graphene oxide to prepare a new type of ternary composite material (β-cyclodextrin/dopamine hydrochloride-graphene oxide, CD-DGO). The material was characterized using scanning electron microscopy, Fourier infrared spectrometry, transmission electron microscopy, and specific surface area optical analysis. Two typical sulfonamides antibiotics (sulfamethoxazole, sulfadiazine) adsorption capacity were evaluated in terms of the dosage of composite materials, the ratio of each component, and the pH of the solution. We analyzed the adsorption characteristics via adsorption kinetics and adsorption isotherms, and then investigated the stability of the adsorbent through desorption and regeneration of the adsorbent. The results show that the adsorption effect of sulfonamides antibiotics is best at pH = 2; the adsorption kinetics conform to the pseudo-second-order kinetic model, and the adsorption equilibrium follows the Langmuir adsorption isotherm; the maximum adsorption capacity of CD-DGO for sulfamethoxazole and sulfadiazine is 144 mg·g−1 and 152 mg·g−1, respectively. The material has good reusability, and the dominant force in the adsorption process is the π-π electron conjugation effect with hydrogen bonding. This offers a theoretical basis for the treatment of sulfonamides antibiotics water pollution.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

Data availability

The datasets used or analyzed during the current study are available from the corresponding author on reasonable request.

References

  • Alsbaiee A, Smith BJ, Xiao LL, Ling YH, Helbling DE, Dichtel WR (2016) Rapid removal of organic micropollutants from water by a porous β-cyclodextrin polymer. Nature 529:190–194

    Article  CAS  Google Scholar 

  • Azhar MR, Abid HR, Periasamy V, Sun HQ, Tade MO, Wang SB (2017) Adsorptive removal of antibiotic sulfonamide by UiO-66 and ZIF-67 for wastewater treatment. J Colloid Interface Sci 500:88–95

    Article  CAS  Google Scholar 

  • Bao XL, Qiang ZM, Chang JH, Ben WW, Qu JH (2014) Synthesis of carbon-coated magnetic nanocomposite (Fe3O4@C) and its application for sulfonamide antibiotics removal from water. J Environ Sci 5:962–969

    Article  Google Scholar 

  • Biošić M, Mitrevski M, Babić S (2017) Environmental behaviour of sulfadiazine, sulfamethazine and their metabolites. Environ Sci Pollut Res 24:9802–9812

    Article  Google Scholar 

  • Chen G, Guan HT, Dong CJ, Wang LD (2016) Hydrothermal synthesis of reduced graphene oxide/nickel oxide composite as electrode materials for supercapacitor. Rare Metal Mat Eng S1:32–37

    Google Scholar 

  • Chen Q, Wang X, Yi P, Zhang P (2021) Key roles of electron cloud density and configuration in the adsorption of sulfonamide antibiotics on carbonaceous materials: molecular dynamics and quantum chemical investigations. Appl Surf Sci 536:147757

    Article  CAS  Google Scholar 

  • Cheng JX, Jiang FH, Zhang SQ (2021) A nanofluidic device for ultrasensitive and label-free detection of tetracycline in association with γ-cyclodextrin and GO. Anal Methods 13:1832–1838

    Article  CAS  Google Scholar 

  • Dan A, Li L, Tai YP, Zhang XM, Tao R, Yang Y (2020) Behavior assessment of sulfonamides and N4-acetyl sulfonamides from wastewater effluent in subsurface constructed wetlands: removal, distribution, and biotransformation. Chem Eng J 396:125252

    Article  Google Scholar 

  • Delparastan P, Malollari KG, Lee H, Messersmith PB (2019) Direct evidence for the polymeric nature of polydopamine. Angew Chem Int Edit 58:1077–1082

    Article  CAS  Google Scholar 

  • Guo YJ, Guo SJ, Ren JT, Zhai YM, Dong SJ, Wang E (2010) Cyclodextrin functionalized graphene nanosheets with high supramolecular recognition capability: synthesis and host-guest inclusion for enhanced electrochemical performance. ACS Nano 4(7):4001–4010

    Article  CAS  Google Scholar 

  • Kim YJ, Young CJ, Ham H, Huh H, So DS, Kang I (2011) Preparation of piezoresistive nano smart hybrid material based on graphene. Curr Appl Phys 11:350–352

    Article  Google Scholar 

  • Li YW, Mo CH, Zhao N, Tai YP, Bao YP, Wang JY, Li MY, Liang WM (2009) Investigation of sulfonamides and tetracyclines antibiotics in soils from various vegetable fields. Environ Sci 30:1762–1766

    CAS  Google Scholar 

  • Liu MC, Chen CL, Hu J, Wu XL, Wang XK (2011) Synthesis of magnetite/graphene oxide composite and application for cobalt (II) removal. J Phys Chem C 115:25234–25240

    Article  CAS  Google Scholar 

  • Liu YB, Peng YL, An BH, Li LC, Liu Y (2019) Effect of molecular structure on the adsorption affinity of sulfonamides onto CNTs: batch experiments and DFT calculations. Chemosphere 246:125778

    Article  Google Scholar 

  • Lv QX, Gong H, Wang R (2018) Synthesis of β-cyclodextrin/epichlorohydrin polymer and its adsorption properties for bisphenol s. Res of Environ Sci 31(11):1933–1939

    Google Scholar 

  • Olivier JP (2001) The characterization of porous materials by gas adsorption methods: a review: the synthesis and characterization of microporous an mesoporous materials. Prepr Pap-Am Chem Soc. Div Fuel Chem 46:34–37

    CAS  Google Scholar 

  • Qi YC, Yang ML, Xu WH, He S, Men Y (2017) Natural polysaccharides-modified graphene oxide for adsorption of organic dyes from aqueous solutions. J Colloid Interface Sci 486:84–96

    Article  CAS  Google Scholar 

  • Ramezanzadeh B, Haeri Z, Ramezanzadeh M (2016) A facile route of making silica nanoparticles-covered graphene oxide nanohybrids (SiO2-GO); fabrication of SiO2-GO/epoxy composite coating with superior barrier and corrosion protection performance. Chem Eng J 303:511–528

    Article  CAS  Google Scholar 

  • Ramli MR, Sulaiman NMN, Mohd MA, Rabuni MF (2015) Performance of chlorination process during nanofiltration of sulfonamide antibiotic. Water Sci Technol 72:1611–1620

    Article  CAS  Google Scholar 

  • Ren XM, Wang YS, He T (2013) Key processes and mechanism for preparing graphene by hummers method. J Mater Eng 1:1–5

    Google Scholar 

  • Rostamian R, Behnejad H (2017) Insights into doxycycline adsorption onto graphene nanosheet: a combined quantum mechanics, thermodynamics, and kinetic study. Environ Sci Pollut Res 25(4):1–10

    Google Scholar 

  • Shen Y, Zhu XY, Chen BL (2016) Size effects of graphene oxide nanosheets on the construction of three-dimensional graphene-based macrostructures as adsorbents. J Mater Chem A4:12106–12118

    Article  Google Scholar 

  • Sheng C, Liu XY, Liu Y, Shen XD, Lin BL, Han GF, Wu ZW (2010) Adsorption properties of nitrobenzene in wastewater with silica aerogels. Sci China Technol Sci 25:3367–2371

    Google Scholar 

  • Silva IS, Feitosa EL, Santos ME, Silva RM, Rocha MS, Da Silva FI, Lima FS, Costa AM, Alves PB, Sousa S, Oliverira AP, Lima SD (2020) Theoretical and experimental investigations on inclusion complex β-cyclodextrin and sulcatone: a cardiovascular activity evaluation. J Braz Chem Soc 31:1064–1077

    CAS  Google Scholar 

  • Sousa IL, Porto CM, Bassani K, Martins MH, Pessine F, Morgon N (2020) Preparation and characterization of the β-cyclodextrin inclusion complex with benzbromarone. J Braz Chem Soc 31:1–12

    Google Scholar 

  • Varela-Fernández R, García-Otero X, Díaz-ToméV RU, López-López M, González-Barcia M, Lema MI, Otero-Espinar FJ (2021) Design, optimization, and characterization of lactoferrin-loaded chitosan/TPP and chitosan/sulfobutylether-β-cyclodextrin nanoparticles as a pharmacological alternative for keratoconus treatment. ACS Appl Mater Inter 13(3):3559–3575

    Article  Google Scholar 

  • Wang JY, Zhang JW, Han LB, Wang JM, Zhu LP, Zeng HB (2021) Graphene-based materials for adsorptive removal of pollutants from water and underlying interaction mechanism. Adv Colloid Interface Sci 289:102360

    Article  CAS  Google Scholar 

  • Yang LH, Qiao B, Xu QM, Liu S, Yuan Y, Cheng JS (2021) Biodegradation of sulfonamide antibiotics through the heterologous expression of laccases from bacteria and investigation of their potential degradation pathways. J Hazard Mater 416:125815

    Article  CAS  Google Scholar 

  • Yang WB, Zheng FF, Xue XX, Lu YP (2011) Investigation into adsorption mechanisms of sulfonamides onto porous adsorbents. J Colloid Interface Sci 362:503–509

    Article  CAS  Google Scholar 

  • Yao YR, Na M, Zhu YQ, Li Y, Li SY (2019) Efficient removal of sulfamerazine (SMR) by ozonation in acetic acid solution after enrichment SMR from water using granular activated carbon. RSC Adv 16:9145–9152

    Article  Google Scholar 

  • Yu JH, Yang LY, Wang LT, Sheng JX, Qiu H (2021) Research progress of polydopamine−based environmental functional materials for the adsorption of the heavy metals in water. Environ Chem 40:2204–2216

    Google Scholar 

  • Zhang MX, Kong MQ, Liu CJ, Huang YJ, Li GX (2018) Toughening of TDE-85 epoxy resin by dopamine-modified graphene oxide. Acta Polym Sin 6:721–732

    Google Scholar 

  • Zhang Q, Xin Q, Zhu JM, Cheng JP (2014) The antibiotic contaminations in the main water bodies in China and the associated environmental and human health impacts. Environ Chem 7:1075–1083

    Google Scholar 

  • Zhang XB, Zhang YC, Ngo HH, Guo WS, Wen HT, Zhang D, Li CC, Qi L (2020) Characterization and sulfonamide antibiotics adsorption capacity of spent coffee grounds based biochar and hydrochar. Sci Total Environ 716:137015

    Article  CAS  Google Scholar 

  • Zhang XQ, Tian B, Li Z, Lv GX (2017) Layered graphene topological structure and performance. Chem Res Appl 29:3–11

    Google Scholar 

  • Zhao WT, Sui Q, Mei XB, Cheng XT (2018) Efficient elimination of sulfonamides by an anaerobic/anoxic/oxic-membrane bioreactor process: performance and influence of redox condition. Sci Total Environ 633:668–676

    Article  CAS  Google Scholar 

  • Zhou LJ, Ying GG, Liu S, Zhao JL, Chen F, Zhang RQ, Peng FQ, Zhang QQ (2012) Simultaneous determination of human and veterinary antibiotics in various environmental matrices by rapid resolution liquid chromatography-electrospray ionization tandem mass spectrometry. J Chromatogr A 1244:123–138

    Article  CAS  Google Scholar 

Download references

Funding

This work was supported by the University Natural Science Research Project of Anhui Province [KJ2019A0827].

Author information

Authors and Affiliations

Authors

Contributions

Hongxia Yu: conceptualization, methodology, formal analysis, writing—original draft. Kun Zheng: validation, resources, investigation. Xiaoying Xu: investigation. Xiaowei Liu: investigation. Bin Zhao: investigation. Haitao Ding: formal analysis. Zhimin Yu: formal analysis, formal analysis. Chengxun Deng: formal analysis, writing—review and editing.

Corresponding author

Correspondence to Chengxun Deng.

Ethics declarations

Competing interests

The authors declare no competing interests.

Additional information

Responsible Editor: Tito Roberto Cadaval Jr

Publisher's note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Highlights

• A ternary composite adsorbent was prepared by modifying graphene oxide with β -cyclodextrin and dopamine.

• This work analyzed two typical sulfonamides antibiotics: sulfamethoxazole and sulfadiazine.

• The adsorption kinetics conform to the pseudo-second-order kinetic equation, and the adsorption equilibrium follows the Langmuir adsorption isotherm.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yu, H., Zheng, K., Xu, X. et al. Preparation of β-cyclodextrin/dopamine hydrochloride-graphene oxide and its adsorption properties for sulfonamide antibiotics. Environ Sci Pollut Res 29, 70192–70201 (2022). https://doi.org/10.1007/s11356-022-20828-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11356-022-20828-4

Keywords

Navigation